Brønsted acidic ionic liquids and their zwitterions: Synthesis, characterization and pKa determination

Chemistry - A European Journal

Volumn 10, Issue 19, 2004, Pages 4886-4893

  Fei, Zhaofu ^a   Zhao, Dongbin ^a   Geldbach, Tilmann J ^a   Scopelliti, Rosario ^a   Dyson, Paul J ^a  

^a EPFL   (Switzerland)

Author keywords

Acidity; Carboxylic acids; Imidazolium salts; Structure elucidation; Zwitterions

Indexed keywords

CHLORIDE MINERALS; HYDROGEN BONDS; MELTING; SINGLE CRYSTALS; TITRATION; X RAY DIFFRACTION ANALYSIS;

ACIDIC IONIC LIQUIDS; SUBSTITUENT GROUPS; ZWITTERIONS;

CARBOXYLIC ACIDS;

AMPHOLYTE; IMIDAZOLE DERIVATIVE;

ACIDITY; ARTICLE; CRYSTAL STRUCTURE; DRUG DETERMINATION; ESTERIFICATION; HYDROGEN BOND; MOLECULAR INTERACTION; PKA; POTENTIOMETRY; PROTON TRANSPORT; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 5444234125     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400145     Document Type: Article

References (64)

1. For leading reviews see a) K R Seddon, J Chem Technol. Biotechnol 1997, 68, 351,
2. b) T Welton, Chem Rev 1999, 99, 2071,
3. c) P Wasserscheid, W. Keim, Angew Chem 2000, 112, 3926; Angew Chem Int Ed. Engl 2000, 39, 3772,
4. c) P Wasserscheid, W. Keim, Angew Chem 2000, 112, 3926; Angew Chem Int Ed. Engl 2000, 39, 3772,
5. d) C M Gordon, Appl Catal A 2001, 222, 101;
6. e) H Olivier-Bourbigou, L Magna, J Mol Catal 2002 182-183, 419;
7. f) D Zhao, M Wu, Y Kou, E Min, Catal Today 2002, 74, 157;
8. g) J Dupont, R. F de Souza, P. A Z Suarez, Chem Rev 2002, 102, 3667
9. Imidazolium salts and variations leading to functionalized ionic liquids J. H Davis, Jr, in Ionic Liquids in Synthesis (Eds. P Wasserscheid, T Welton), Wiley-VCH, Weinheim, 2003, Chapter 2, p 33.
10. W. A Herrmann, C Kocher, L J. Goossen, G. R J Artus, Chem Eur J 1996, 2, 1627
11. K.-M Lee, Y-T-Y Lee, J B Lin, J Mater. Chem 2003, 13, 1079.
12. L. C Branco, J N Rosa, J. J Moura Ramos, C A M Alfons, Chem Eur J 2002, 8, 3671
13. a) D J Brauer, K. Kottsieper, C Liek, O. Stelzer, H Waffenschmidt, P. Wasserscheid, J Organomet Chem 2001, 630, 177,
14. b) R P J Bronger, M. S Silva, P. C J. Kamer, P W. N M. van Leeuwen, Chem Commun. 2002, 3044
15. T L Merrigan, E. D. Bates, S C Dorman, J H Davis, Jr., Chem Commun 2000, 2051
16. A C Cole, J L Jensen, I. Ntai, K L T Tran, K. J. Weaver, D. C Forbes, J H. Davis, Jr., J Am Chem Soc 2002, 124, 5962.
17. N Gathergood, P. J Scammells, Aust J Chem 2002, 55, 557
18. D. S. McGuinness, K J Cavell, Organometallics 2000, 19, 741.
19. W A Herrmann, L J Goossen, M. Spiegler, J Organomet Chem 1997, 547, 357
20. a) E Alcalde, M Gisbert, L. Perez-Garcia, Heterocycles 1996, 4, 567,
21. b) V Barboiu, E Streba, M. N Holerca, C. Luca, J Macromol Sci Pure Appl Chem 1995, A32, 1385,
22. c) E Alcalde, M Gisbert, L. Perez-Garcia, Chem. Lett 1992, 12, 2357;
23. d) G M. Blackburn, H L H Dodds, J Chem. Soc. Perkin Trans 2, 1974, 377.
24. a) T. Watanabe (Fuji Photo Film Co, Ltd, Japan), Jpn Kokai Tokkyo Koho JKXXAF JP 2003017148 A2 20030117, 2001 [Application. JP 2001-20409020010704];
25. L Goossen, M. Hendrix (Bayer AG, Germany), Eur. Pat. Appl. EPXXDW EP 1157995 A2 20011128, 2001 [Application. EP 2001-11117720010511]
26. G M Blackburn, H L H. Dodds, J Chem Soc Perkin Trans 2, 1974, 377
27. a) J. Velisek, T. Davidek, J Davidek, Maillard Reaction in Foods and Medicine, RSC Special Publication 223, Royal Society of Chemistry, Cambridge, 1998, pp. 204-208;
28. b) J. Velisek, T. Davidek, J Davidek, Lebensm -Wiss Technol 1992, 25, 74,
29. c) T. Davidek, J. Velisek, J. Davidek, P Pech, J Agric Food Chem 1991, 39, 1374.
30. J Velisek, T Davidek, J. Davidek, P Trska, F Kvasnicka, K. Velcova, J Food Sci 1989, 54, 1544.
31. B Kratochvil, J. Ondracek, J. Velisek, J. Hasek, Acta Crystallogr. Sect C 1988, 44, 1579
32. a) N Kuhn, H. Bohnen, G. Henkel, Z Naturforsch Teil B 1994, 49, 1473,
33. b) N Kuhn, E Niquet, M. Steinmann, I Walker, Z Naturforsch Teil B 1999, 54, 1181,
34. c) L. L. Borer, J V Kong, E. Oram, Acta Crystallogr Sect C 1989, 45, 1169.
35. J D Holbrey, W M Reichert, I Tkatchenko, E Bouajila, O Walter, I. Tommasi, R. D. Rogers, Chem Commun 2003, 28.
36. "Ionic Liquids as Green Solvents Progress and Prospects". M Aresta, I Tkatchenko, I. Tommasi, ACS Symp. Ser 2003, 856, 93
37. H. A Duong, T. N Tekavec, A M Arif, J Louie, Chem Commun 2004, 112.
38. K J Harlow, A. F Hill, T. Welton, Synthesis 1996, 697.
39. a) P. B Hitchcock, K. R. Seddon, T Welton, J Chem Soc. Dalton Trans 1993, 2639;
40. b) P. A. Z. Suarez, J E. L Dullius, S. Einloft, R F de Souza, J. Dupont, Polyhedron 1996, 15, 1217.
41. P J Dyson, J S McIndoe, D Zhao, Chem Commun 2003, 508
42. a) A. Elaiwi, P B Hitchcock, K R Seddon, N Srinivasan, Y M. Tan, T. Welton, J. A. Zora, J. Chem Soc Dalton Trans 1995, 3467,
43. b) J. J Golding, D R MacFarlaine, L. Spiccia, M Forsyth, B W Skelton, A. H. White, Chem. Commun 1998, 1593;
44. c) J. Fuller, R T Carlin, H C De Long, D. Haworth, J Chem Soc Chem Commun 1994, 229
45. A. Horváth, Synthesis 1995, 1183
46. J S Wilkes, M. J Zaworotko, J Chem. Soc Chem Commun 1992, 965
47. J. Fuller, R T Carlin, Proc Electrochem Soc 1999, 98, 277.
48. P Bonhôte, A -P Dias, N. Papageorgiou, K. Kalyanasundaram, M Gratzel, Inorg Chem 1996, 35, 1168
49. a) P J Dyson, D. J. Ellis, W Henderson, G Laurenczy, Adv Synth Catal 2003, 345, 216,
50. b) I Billard, G. Moutiers, A Labet, A El Azzi, C Gaillard, C. Mariet, K. Lutzenkirchen, Inorg Chem 2003, 42, 1726.
51. For a summary of factors influencing the melting point, see, for example J. D. Holbrey, R. D. Rogers, in Ionic Liquids in Synthesis (Eds P Wasserscheid, T Welton), Wiley-VCH, Weinheim, 2003, Chapters, p 41.
52. a values can be found in a) J March, Advanced Organic Chemistry-Reactions, Mechanisms and Structure, 4th ed, Wiley-Interscience, New York, 1992, Chapter 8,
53. b) R Stewart, The Proton: Applications to Organic Chemistry Organic Chemistry, A Series of Monographs, Vol 46 (Ed H H Wasserman), Academic Press, New York, 1985.
54. a) C O Silva, E C da Silva, M. A Chaer Nascimento, J. Phys Chem A 2000, 104, 2402,
55. b) C. O daSilva, E C. da Silva, M. A. Chaer Nascimento, J Phys Chem. A 1999, 103, 11194.
56. G Schurmann, M Cossi, V. Barone, J Tomasi, J Phys. Chem A 1998, 102, 6706
57. D R. Lide, CRC Handbook of Chemistry and Physics, 78th ed, CRC Press, Boca Raton, 1997-1998
58. M Picquet, I Tkatchenko, I Tommasi, P. Wasserscheid, J Zimmermann, Adv. Synth Catal 2003, 345, 959
59. P. J. Dyson, M C Grossel, N Srinivasan, T. Vine, T. Welton, D J Williams, A J White, T. Zigras, J Chem Soc Dalton Trans 1997, 3465
60. P. J Dyson, J S McIndoe, Inorg Chim Acta 2003, 354, 68.
61. A Albert, E P. Serjeant, The Determination of Ionization Constants A Laboratory Manual, 3rd ed, Chapman and Hall, New York, 1984.
62. G M. Sheldrick, SHELX-97 Structure Solution and Refinement Package, University of Gottingen, Gottingen (Germany), 1997
63. L J Farrugia, J. Appl Crystallogr 1997, 30, 565
64. N Walker, D Stuart, Acta Crystallogr Sect. A 1983, 39, 158.